WO1995024388A1 - A method for the preparation of aqueous solutions containing performic acid as well as their use - Google Patents
A method for the preparation of aqueous solutions containing performic acid as well as their use Download PDFInfo
- Publication number
- WO1995024388A1 WO1995024388A1 PCT/NL1994/000059 NL9400059W WO9524388A1 WO 1995024388 A1 WO1995024388 A1 WO 1995024388A1 NL 9400059 W NL9400059 W NL 9400059W WO 9524388 A1 WO9524388 A1 WO 9524388A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- carboxylic acid
- acid
- aqueous solutions
- ester
- Prior art date
Links
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000000243 solution Substances 0.000 claims abstract description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000019253 formic acid Nutrition 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 7
- 125000004185 ester group Chemical group 0.000 claims abstract description 7
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 238000004659 sterilization and disinfection Methods 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000011012 sanitization Methods 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 150000005846 sugar alcohols Chemical class 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 5
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- -1 ester compounds Chemical class 0.000 description 3
- 235000013773 glyceryl triacetate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000002371 mycocidal effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 230000003330 sporicidal effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Definitions
- the present invention relates to a method for the preparation of aqueous solutions containing performic acid formed by reaction of formic acid and hydrogen peroxide in the presence of a catalyst.
- the present invention relates to a method for the preparation of aqueous solutions containing performic acid formed by reaction of formic acid and hydrogen peroxide in the presence of a catalyst, characterized in that the catalyst is a compound containing at least one ester group and/or 0 • C-0- roup differing from a carboxylic acid group.
- the compound may be used in catalytic amounts, which expression is well-known to men skilled in the art. However, it is preferred that a minimum amount of 10 ppm, calculated on the aqueous solution, is used. In general an amount of more than 10.000 ppm will not bring additional advantages. The particularly preferred range is 200-5000 ppm, again calculated on the total aqueous solution containing the reactants.
- the catalytic compound is a carboxylic acid ester which is not toxic. However, other ester compounds such as sulfate esters, sulfonate esters/lactones and phosphate esters and similar compounds may be successfully used.
- the catalytic compound is selected from the group consisting of carboxylic acid esters where the carboxylic acid is: a) aromatic or aliphatic C 1 -C 20 carboxylic acid; b) aromatic or aliphatic di- or pol functional carboxylic acid; and wherein the alcohol part is a) aliphatic or aromatic C ⁇ -C ⁇ mono- of polyfunctional alcohol, b) sugar alcohol , c) polymer containing hydroxyl groups .
- Suitable are a.o. compounds like glyceryl mono-, di- and tri- esters, wherein the carboxylic acid is C-r-Cgo carboxylic acid, poly- mers such as (partially hydrolysed) polyvinylacetate.
- the use of the catalyst in accordance with the invention causes an enormous increase, e.g. of 100-300 % of the concentration of performic acid. Consequently, performic acid containing preparations prepared in accordance with the invention are more efficient than the prior art solutions.
- the present invention also relates to an aqueous solution containing performic acid, formic acid, hydrogen peroxide as well as a compound containing at least one ester group and/or 0
- the invention relates to the use of the above aqueous solutions of the invention for sterilization, sanitization and disinfection purposes.
- reference is e.g. made to the above cited EP-A-0231 623 and NL 9300445. It appeared from many tests that any compound of the ester type may be used with a certain degree of success. An average chemist will immediately understand what is meant by "ester type”.
- the inventors find the effect of the ester type compound on the amount of performic acid in the solution surprising.
- the invention is explained in more detail in the following examples.
- caproic acid mono- and diglyceride (Grinstedt TS-T 104)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/704,573 US6049002A (en) | 1994-03-09 | 1994-03-09 | Method for the preparation of aqueous solutions containing performic acid as well as their use |
AU62649/94A AU6264994A (en) | 1994-03-09 | 1994-03-09 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
ES94910062T ES2131679T3 (en) | 1994-03-09 | 1994-03-09 | PROCEDURE FOR THE PREPARATION OF AQUEOUS SOLUTIONS CONTAINING PERFORMIC ACID, AS WELL AS ITS USE. |
PCT/NL1994/000059 WO1995024388A1 (en) | 1994-03-09 | 1994-03-09 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
DE69418903T DE69418903T2 (en) | 1994-03-09 | 1994-03-09 | METHOD FOR PRODUCING AQUEOUS PERFORMIC ACID SOLUTIONS AND USE THEREOF |
CA002185100A CA2185100C (en) | 1994-03-09 | 1994-03-09 | A method for preparation of aqueous solutions containing performic acid as well as their use |
EP94910062A EP0751933B1 (en) | 1994-03-09 | 1994-03-09 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
FI963469A FI119188B (en) | 1994-03-09 | 1996-09-04 | Process for the preparation of aqueous solutions containing permic acid and their use |
HK98111134A HK1010365A1 (en) | 1994-03-09 | 1998-10-08 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/NL1994/000059 WO1995024388A1 (en) | 1994-03-09 | 1994-03-09 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995024388A1 true WO1995024388A1 (en) | 1995-09-14 |
Family
ID=19863700
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NL1994/000059 WO1995024388A1 (en) | 1994-03-09 | 1994-03-09 | A method for the preparation of aqueous solutions containing performic acid as well as their use |
Country Status (9)
Country | Link |
---|---|
US (1) | US6049002A (en) |
EP (1) | EP0751933B1 (en) |
AU (1) | AU6264994A (en) |
CA (1) | CA2185100C (en) |
DE (1) | DE69418903T2 (en) |
ES (1) | ES2131679T3 (en) |
FI (1) | FI119188B (en) |
HK (1) | HK1010365A1 (en) |
WO (1) | WO1995024388A1 (en) |
Cited By (10)
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US5589507A (en) * | 1995-11-17 | 1996-12-31 | Minntech Corporation | Method for sterilizing medical devices utilizing a room temperature sterilant |
EP0762831A1 (en) * | 1994-06-01 | 1997-03-19 | Minntech Corporation | Room temperature sterilant |
WO1997019594A1 (en) * | 1995-12-01 | 1997-06-05 | Minntech Corporation | Room temperature sterilant for medical devices |
US6211237B1 (en) | 1998-03-23 | 2001-04-03 | Degussa-Huls Ag | Aqueous disinfecting agent containing performic acid and peracetic acid process for production and process for use thereof |
US6632397B1 (en) | 1998-10-01 | 2003-10-14 | Minntech Corporation | Multi-part anti-microbial concentrate system, activated solution, use-dilution solution, method of making same, and method of sterilizing with the use-dilution solution |
WO2012037294A2 (en) * | 2010-09-14 | 2012-03-22 | Pimi Agro Cleantech Ltd. (Israel) | Compositions and methods of treating edible matter and substrates therefor |
US9518013B2 (en) | 2014-12-18 | 2016-12-13 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US9845290B2 (en) | 2014-12-18 | 2017-12-19 | Ecolab Usa Inc. | Methods for forming peroxyformic acid and uses thereof |
US11040902B2 (en) | 2014-12-18 | 2021-06-22 | Ecolab Usa Inc. | Use of percarboxylic acids for scale prevention in treatment systems |
US11260040B2 (en) | 2018-06-15 | 2022-03-01 | Ecolab Usa Inc. | On site generated performic acid compositions for teat treatment |
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US7150884B1 (en) | 2000-07-12 | 2006-12-19 | Ecolab Inc. | Composition for inhibition of microbial growth |
US6479454B1 (en) | 2000-10-05 | 2002-11-12 | Ecolab Inc. | Antimicrobial compositions and methods containing hydrogen peroxide and octyl amine oxide |
US7316824B2 (en) * | 2000-12-15 | 2008-01-08 | Ecolab Inc. | Method and composition for washing poultry during processing |
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US6964787B2 (en) * | 2001-02-01 | 2005-11-15 | Ecolab Inc. | Method and system for reducing microbial burden on a food product |
AU2002250386A1 (en) * | 2001-03-22 | 2002-10-08 | Pioneer Hi-Bred International, Inc. | Expansin protein and polynucleotides and methods of use |
US6635286B2 (en) * | 2001-06-29 | 2003-10-21 | Ecolab Inc. | Peroxy acid treatment to control pathogenic organisms on growing plants |
US6627593B2 (en) | 2001-07-13 | 2003-09-30 | Ecolab Inc. | High concentration monoester peroxy dicarboxylic acid compositions, use solutions, and methods employing them |
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US7754670B2 (en) | 2005-07-06 | 2010-07-13 | Ecolab Inc. | Surfactant peroxycarboxylic acid compositions |
US8075857B2 (en) * | 2006-10-18 | 2011-12-13 | Ecolab Usa Inc. | Apparatus and method for making a peroxycarboxylic acid |
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US8871807B2 (en) | 2008-03-28 | 2014-10-28 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
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US8956161B2 (en) | 2008-11-04 | 2015-02-17 | Duane C Keller | Article and method for controlling oral-originated systemic disease |
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US8591229B2 (en) | 2010-12-16 | 2013-11-26 | Duane C. Keller | Devices and methods for creating a positive pressure environment for treatment of oral biofilms associated with periodontal disease |
US20140039050A1 (en) | 2011-02-24 | 2014-02-06 | Marcelo Moreira da Costa | Method for preventing bacterial infection in a fermentation process |
US9321664B2 (en) | 2011-12-20 | 2016-04-26 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
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US9752105B2 (en) | 2012-09-13 | 2017-09-05 | Ecolab Usa Inc. | Two step method of cleaning, sanitizing, and rinsing a surface |
US20140308162A1 (en) | 2013-04-15 | 2014-10-16 | Ecolab Usa Inc. | Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing |
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US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
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US10172351B2 (en) | 2015-09-04 | 2019-01-08 | Ecolab Usa Inc. | Performic acid on-site generator and formulator |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2008896A1 (en) * | 1968-05-20 | 1970-01-30 | Petrocarbon Dev Ltd | |
DE1962671A1 (en) * | 1969-12-13 | 1971-06-24 | Degussa | Process for the production of percarboxylic acid |
FR2101175A1 (en) * | 1970-08-01 | 1972-03-31 | Bayer Ag | |
SU1172514A1 (en) * | 1983-10-05 | 1985-08-15 | Тартусский Ордена Трудового Красного Знамени И Ордена Дружбы Народов Государственный Университет | Method of obtaining desinfection agent |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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DE3320219A1 (en) * | 1983-06-03 | 1984-12-06 | Henkel KGaA, 4000 Düsseldorf | CONTINUOUS, CATALYTIC EPOXIDATION OF DOUBLE OLEFINIC BINDINGS WITH HYDROGEN PEROXIDE AND FORMIC ACID |
-
1994
- 1994-03-09 EP EP94910062A patent/EP0751933B1/en not_active Expired - Lifetime
- 1994-03-09 US US08/704,573 patent/US6049002A/en not_active Expired - Fee Related
- 1994-03-09 WO PCT/NL1994/000059 patent/WO1995024388A1/en active IP Right Grant
- 1994-03-09 AU AU62649/94A patent/AU6264994A/en not_active Abandoned
- 1994-03-09 ES ES94910062T patent/ES2131679T3/en not_active Expired - Lifetime
- 1994-03-09 DE DE69418903T patent/DE69418903T2/en not_active Expired - Lifetime
- 1994-03-09 CA CA002185100A patent/CA2185100C/en not_active Expired - Fee Related
-
1996
- 1996-09-04 FI FI963469A patent/FI119188B/en not_active IP Right Cessation
-
1998
- 1998-10-08 HK HK98111134A patent/HK1010365A1/en not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2008896A1 (en) * | 1968-05-20 | 1970-01-30 | Petrocarbon Dev Ltd | |
DE1962671A1 (en) * | 1969-12-13 | 1971-06-24 | Degussa | Process for the production of percarboxylic acid |
FR2101175A1 (en) * | 1970-08-01 | 1972-03-31 | Bayer Ag | |
SU1172514A1 (en) * | 1983-10-05 | 1985-08-15 | Тартусский Ордена Трудового Красного Знамени И Ордена Дружбы Народов Государственный Университет | Method of obtaining desinfection agent |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 8609, Derwent World Patents Index; AN 86-060814 * |
Cited By (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0762831A4 (en) * | 1994-06-01 | 1999-06-16 | Minntech Corp | Room temperature sterilant |
EP0762831A1 (en) * | 1994-06-01 | 1997-03-19 | Minntech Corporation | Room temperature sterilant |
US5616616A (en) * | 1994-06-01 | 1997-04-01 | Minntech Corporation | Room Temperature sterilant |
EP0881876A1 (en) * | 1995-11-17 | 1998-12-09 | Minntech Corporation | Method for reprocessing medical devices utilizing a room temperature sterilant |
US5589507A (en) * | 1995-11-17 | 1996-12-31 | Minntech Corporation | Method for sterilizing medical devices utilizing a room temperature sterilant |
AU706306B2 (en) * | 1995-11-17 | 1999-06-10 | Minntech Corporation | Method for reprocessing medical devices utilizing a room temperature sterilant |
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Also Published As
Publication number | Publication date |
---|---|
EP0751933A1 (en) | 1997-01-08 |
FI119188B (en) | 2008-08-29 |
ES2131679T3 (en) | 1999-08-01 |
US6049002A (en) | 2000-04-11 |
HK1010365A1 (en) | 1999-06-17 |
DE69418903D1 (en) | 1999-07-08 |
AU6264994A (en) | 1995-09-25 |
CA2185100A1 (en) | 1995-09-14 |
CA2185100C (en) | 2006-10-31 |
EP0751933B1 (en) | 1999-06-02 |
FI963469A0 (en) | 1996-09-04 |
DE69418903T2 (en) | 1999-12-02 |
FI963469A (en) | 1996-09-04 |
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